Photocatalytic synthesis method of trifluoromethyl-containing benzodihydropyran-4-one compound

Abstract

The invention discloses a photocatalytic synthesis method of a trifluoromethyl-containing benzodihydropyran-4-ketone compound, which comprises the following steps: reacting a 2-allyloxy benzaldehyde compound shown as a chemical structural general formula (I) with sodium trifluoromethanesulfinate in an organic solvent under the irradiation of visible light to obtain the trifluoromethyl-containing benzodihydropyran-4-ketone compound. The benzodihydropyran-4-ketone compound containing trifluoromethyl is obtained, and the structural general formula of the benzodihydropyran-4-ketone compound containing trifluoromethyl is shown in a formula (II). The synthesis method provided by the invention adopts low-cost sodium trifluoromethanesulfinate as a raw material, does not need to additionally add a transition metal catalyst, a photocatalyst, an oxidizing agent and the like, and has the characteristics of mild reaction conditions, simple synthesis and post-treatment processes, high reaction atomic efficiency, high target product yield, low preparation cost, environmental friendliness and the like; the method is suitable for large-scale industrial production application.

Description

Technical Field

[0001] The invention belongs to the technical field of organic compound synthesis, and particularly relates to a photocatalytic synthesis method of chroman-4-one compounds containing trifluoromethyl. Background Art

[0002] Chromane-4-one compounds are often used as drug intermediates because of their strong biological activity. They can be efficiently prepared into antipsychotic, antitumor, and anticancer drugs, so they play an important role in the fields of biology and medicine. Trifluoromethyl is an important active functional group. Related studies have shown that the introduction of trifluoromethyl functional groups into the skeleton of heterocyclic compounds can give heterocyclic compounds new pharmacological activities.

[0003] At present, there are relevant reports on the synthesis of trifluoromethyl-containing chroman-4-one compounds. For example, Zhu Gangguo of Zhejiang Normal University disclosed that 2-allyloxybenzaldehyde and Togni reagent reacted under the catalysis of Cu(MeCN)4PF6 to obtain trifluoromethyl-containing chroman-4-one compounds (Chem. Commun., 2017, 53, 6440-6443, the synthesis route is shown in Figure 1 ). However, this method has problems such as low yield, high synthesis cost, and the need to use expensive Togni reagent as a trifluoromethyl source. Zheng Lingyun of Xinyang Normal University disclosed that 2-allyloxybenzaldehyde and sodium trifluoromethylsulfinate react with 3 equivalents of potassium persulfate as an oxidant at a temperature of 100°C to obtain a trifluoromethyl-containing chroman-4-one compound (Org. Lett. 2018, 20, 6520-6525). The synthesis route is shown in Figure 1 ). However, this method needs to be carried out under high temperature conditions and requires the use of a large excess of oxidant, which not only has low atom utilization and low reaction efficiency, but also has great difficulty in product separation and high preparation cost. Summary of the invention

[0004] In view of the problems existing in the prior art, the present invention aims to provide a photocatalytic synthesis method of chroman-4-one compounds containing trifluoromethyl.

[0005] In order to achieve the above object, the present invention adopts the following technical solution:

[0006] A photocatalytic synthesis method of a trifluoromethyl-containing chroman-4-one compound comprises the following steps: reacting a 2-allyloxybenzaldehyde compound having a general chemical structure as shown in (I) and sodium trifluoromethylsulfinate in an organic solvent under visible light irradiation to obtain a trifluoromethyl-containing chroman-4-one compound having a general chemical structure as shown in (II);

[0007]

[0008] Among them, R 1 The number of is 1 to 3, which may be the same or different, and the position on the benzene ring is not limited, and is selected from hydrogen, C1 to C5 alkyl, C1 to C5 alkoxy, halogen, nitro or ester.

[0009] Preferably, the C1-C5 alkyl group may be a C1-C5 alkyl group substituted with a substituent or an unsubstituted C1-C5 alkyl group, for example, selected from methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, isobutyl, trifluoromethyl and the like.

[0010] Preferably, the C1-C5 alkoxy group may be a C1-C5 alkoxy group substituted with a substituent or an unsubstituted C1-C5 alkoxy group, for example, selected from methoxy, ethoxy, trifluoromethoxy, benzyloxy and the like.

[0011] Preferably, the halogen is selected from F, Cl or Br.

[0012] Preferably, the ester group is selected from methyl formate or ethyl formate.

[0013] Preferably, the molar ratio of the 2-allyloxybenzaldehyde compound to sodium trifluoromethanesulfinate is 1:1.3-1.7.

[0014] Preferably, the visible light is violet light or blue light, more preferably violet light.

[0015] Preferably, the purple light is provided by a 3-10W LED purple light source, more preferably a 5-8W LED purple light source, and particularly preferably an 8W LED purple light source.

[0016] Preferably, the organic solvent is any one of N,N-dimethylformamide, dimethyl sulfoxide, acetone, ethyl acetate, 1,2-dichloroethane, and tetrahydrofuran, and more preferably dimethyl sulfoxide.

[0017] Preferably, the reaction is carried out at room temperature for 12 to 14 hours.

[0018] Compared with the prior art, the present invention has the following beneficial effects:

[0019] (1) The synthesis method of the present invention uses low-cost sodium trifluoromethanesulfinate as a raw material, and does not require the addition of additional transition metal catalysts, photocatalysts, oxidants, etc., which greatly reduces the synthesis cost.

[0020] (2) The 2-allyloxybenzaldehyde compounds used in the synthesis method of the present invention have good functional group compatibility and can be reacted with sodium trifluoromethylsulfinate at room temperature to obtain trifluoromethyl-containing chroman-4-one compounds.

[0021] (3) The synthesis method of the present invention is a one-pot reaction, which has the characteristics of simple synthesis and post-processing process, high reaction atomic efficiency, high yield of target product, low cost, and environmental friendliness, and is suitable for large-scale industrial production and application. BRIEF DESCRIPTION OF THE DRAWINGS

[0022] In order to more clearly illustrate the technical solutions in the embodiments of the present invention, the drawings required for use in the embodiments will be briefly introduced below. Obviously, the drawings described below are only some embodiments of the present invention. For ordinary technicians in this field, other drawings can be obtained based on these drawings without paying creative work.

[0023] Figure 1 A synthetic route for preparing trifluoromethyl-containing chroman-4-one compounds in the prior art;

[0024] Figure 2 A synthetic route diagram of trifluoromethyl-containing chroman-4-one compounds provided by the present invention;

[0025] Figure 3 is the H NMR spectrum of 3-trifluoromethylchroman-4-one prepared in Example 1;

[0026] Figure 4 is the carbon nuclear magnetic resonance spectrum of 3-trifluoromethylchroman-4-one prepared in Example 1;

[0027] Figure 5 This is the nuclear magnetic resonance fluorine spectrum of 3-trifluoromethylchroman-4-one prepared in Example 1. DETAILED DESCRIPTION

[0028] In the following description, for the purpose of illustration rather than limitation, specific details such as specific system structures and technologies are provided to provide a thorough understanding of the embodiments of the present invention. However, it should be clear to those skilled in the art that the present invention may also be implemented in other embodiments without these specific details.

[0029] Example 1

[0030] Reference Figure 2, which is a synthetic route for trifluoromethyl-containing chroman-4-one compounds, preparing compound 1: 3-(2,2,2-trifluoroethyl)chroman-4-one, 3-trifluoromethylchroman-4-one, whose structural formula is as follows:

[0031]

[0032] The specific steps are as follows: 2-allyloxybenzaldehyde (0.3mmol), sodium trifluoromethanesulfinate (0.45mmol) and DMSO (1mL) are added to a 10mL quartz reaction tube in sequence; the resulting mixture is stirred at room temperature under 8W purple light irradiation; the reaction progress is monitored by thin layer chromatography, and after 12h of reaction, 10mL of water is added to the reaction mixture, and 15mL of ethyl acetate is used to extract three times, the organic phases are combined and washed with saturated brine, dried, vacuum concentrated, and purified by column chromatography to obtain compound 1 with a yield of 92%. Compound 1 was characterized, and the obtained nuclear magnetic hydrogen spectrum, carbon spectrum, and fluorine spectrum were shown in Figure 3-5 .

[0033] 1 H NMR(400MHz, CDCl3)δ7.82(d,J=7.9Hz,1H),7.43(t,J=7.8Hz,1H),7.01-6.87(m,2H), 4.64(dd,J=11.4,5.1Hz,1H),4.16(t,J=11.7Hz,1H),3.18-2.92(m,2H),2.00(m,1H).

[0034] 13 C NMR(100MHz, CDCl3)δ190.7,161.5,136.3,127.5(q,J=275.0Hz),121.7,120 .0,117.9,117.8,69.7(q,J=2.0Hz),40.6(q,J=2.0Hz),29.6(q,J=30.0Hz).

[0035] 19 F NMR (376MHz, CDCl3) δ-64.03.

[0036] Example 2

[0037] Preparation of compound 2: 7-methyl-3-(2,2,2-trifluoroethyl)chroman-4-one, 7-methyl-3-(2,2,2-trifluoroethyl)chroman-4-one, the structural formula of which is as follows:

[0038]

[0039] Specific steps: basically the same as those in Example 1, except that 2-allyloxy-4-methylbenzaldehyde is used to replace 2-allyloxybenzaldehyde in Example 1. Yield: 93%.

[0040] 1 H NMR (400MHz, CDCl3) δ7.78(d,J=8.0Hz,1H),6.86(dd,J=8.1,1.5Hz,1H),6.79(s,1H),4.68( dd,J=11.6,5.0Hz,1H),4.20(t,J=11.6Hz,1H),3.17-2.99(m,2H),2.36(s,3H),2.00(m,1H).

[0041] 13 C NMR (100MHz, CDCl3) δ190.3, 161.6, 148.1, 128.0, 127.5 (q, J = 286.4Hz), 123.2, 117.9, 117.8, 69.4 (d, J = 1.4Hz), 40.6 (q, J = 3.0Hz), 29.6 (q, J = 30.0Hz), 21.96.

[0042] 19 F NMR (376MHz,CDCl3)δ-64.02.

[0043] Example 3

[0044] Compound 3: 6-methyl-3-(2,2,2-trifluoroethyl)chroman-4-one; its structural formula is as follows:

[0045]

[0046] Specific steps: basically the same as those in Example 1, except that 2-allyloxy-5-methylbenzaldehyde is used to replace 2-allyloxybenzaldehyde in Example 1. Yield: 85%.

[0047] 1 H NMR (400MHz, CDCl3) δ7.60 (s, 1H), 7.23 (d, J = 8.4Hz, 1H), 6.81 (d, J = 8.5Hz, 1H), 4.60 (dd, J=11.4,5.1Hz,1H),4.12(t,J=11.7Hz,1H),3.14-2.89(m,2H),2.23(s,3H),1.99(m,1H).

[0048] 13 C NMR (100MHz, CDCl3) δ190.9,159.6,137.4,131.2,127.1,126.6(q,J=270.0Hz),11 9.6,117.6,69.6(q,J=2.0Hz),40.5(q,J=2.0Hz),29.6(q,J=30.0Hz),21.9,20.3.

[0049] 19 F NMR (376MHz, CDCl3) δ-64.03.

[0050] Example 4

[0051] Preparation of compound 4: 7-fluoro-3-(2,2,2-trifluoroethyl)chroman-4-one, 7-methyl-3-(2,2,2-trifluoroethyl)chroman-4-one; its structural formula is as follows:

[0052]

[0053] Specific steps: basically the same as those in Example 1, except that 2-allyloxy-4-fluorobenzaldehyde is used to replace 2-allyloxybenzaldehyde in Example 1. Yield: 94%

[0054] 1 H NMR (400MHz, CDCl3) δ7.95-7.79(m,1H),6.69(m,1H),6.61(m,1H),4.66(dd,J=11.5,5.2Hz,1H),4.18(t,J=11.8Hz,1H),3.03(m,2H),2.00(m,1H).

[0055] 13 C NMR (100MHz, CDCl3) δ 189.3, 167.6 (d, J = 255.0Hz), 163.2 (d, J = 14.0Hz), 130.2 (d, J = 11.0Hz), 126.5 (q, J = 274.0Hz), 1 16.9(d,J=3.0Hz), 110.3(d,J=23.0Hz), 104.7(d,J=25.0Hz), 70.1(q,J=2.0Hz), 40.2(q,J=2.0Hz), 29.5(q,J=30Hz).

[0056] 19 F NMR(376MHz, CDCl3)δ-64.06,-99.53.

[0057] Example 5

[0058] Preparation of compound 5: 6-methoxy-3-(2,2,2-trifluoroethyl)chroman-4-one;

[0059]

[0060] Specific steps: basically the same as those in Example 1, except that 2-allyloxy-5-methoxybenzaldehyde is used to replace 2-allyloxybenzaldehyde in Example 1. Yield: 87%

[0061] 1 H NMR (400MHz, CDCl3) δ7.24(d,J=2.8Hz,1H),7.05(m,1H),6.86(d,J=9.0Hz,1H),4.60(dd, J=11.4,5.0Hz,1H),4.13(t,J=11.8Hz,1H),3.73(s,3H),3.12-2.92(m,2H),2.02(m,1H).

[0062] 13 C NMR (100MHz, CDCl3) δ190.8,156.3,154.3,125.7,126.6(q,J=274.0Hz),119.8,119.2,107.7,69.9,55.83,40.51,29.7(29.5(q,J=30Hz).

[0063] 19 F NMR (376MHz,CDCl3)δ-63.99.

[0064] Example 6

[0065] Compound 6: 5-(tert-butyl)-3-(2,2,2-trifluoroethyl)chroman-4-one;

[0066]

[0067] Specific steps: basically the same as those in Example 1, except that 2-allyloxy-6-tert-butylbenzaldehyde is used to replace 2-allyloxybenzaldehyde in Example 1. Yield 90%

[0068] 1H NMR (400MHz, CDCl3) δ7.72 (dd, J=7.8, 1.7Hz, 1H), 7.42 (dd, J=7.6, 1.7Hz, 1H), 6.90 (t, J=7.7Hz, 1H) ,4.71(dd,J=11.3,5.1Hz,1H),4.14(t,J=11.7Hz,1H),3.16-2.91(m,2H),2.00(m,1H),1.31(s,9H).

[0069] 13 C NMR (100MHz, CDCl3) δ191.3,160.7,139.0,133.3,126.7(q,J=275.0Hz),125.7,12 1.3,120.8,69.3(q,J=2.0Hz),40.4(q,J=2.0Hz),34.9,29.7(q,J=30.0Hz),29.6.

[0070] 19 F NMR (376MHz,CDCl3)δ-63.93.

[0071] Example 7

[0072] Compound 7: methyl 4-oxo-3-(2,2,2-trifluoroethyl)chromane-7-carboxylate, methyl 4-oxo-3-(2,2,2-trifluoroethyl)chromane-7-carboxylate;

[0073]

[0074] Specific steps: The steps are basically the same as those in Example 1, except that 3-allyloxy-4-formylbenzoic acid methyl ester is used to replace 2-allyloxybenzaldehyde in Example 1. The yield is 93%.

[0075] 1 H NMR (400MHz, CDCl3) δ8.51(s,1H),8.09(d,J=8.4Hz,1H),6.97(d,J=8.7Hz,1H),4.72(dd,J= 11.6,5.3Hz,1H),4.22(t,J=11.9Hz,1H),3.84(s,3H),3.20-2.96(m,2H),2.14-1.90(m,1H).

[0076] 13C NMR (100MHz, CDCl3) δ189.7,165.7,164.5,137.1,129.9,126.5(q,J=275.0Hz),12 4.1,119.6,118.2,69.9(q,J=2.0Hz),52.2,40.3(q,J=3.0Hz),29.5(q,J=30.0Hz).

[0077] 19 F NMR (376MHz,CDCl3)δ-64.02.

[0078] Example 8

[0079] Compound 8: 6-nitro-3-(2,2,2-trifluoroethyl)chroman-4-one;

[0080]

[0081] The steps are basically the same as those in Example 1, except that 2-allyloxy-5-nitrobenzaldehyde is used to replace the 2-allyloxybenzaldehyde in Example 1. The yield is 95%.

[0082] 1 H NMR (400MHz, CDCl3) δ8.71(d,J=2.8Hz,1H),8.29(dd,J=9.2,2.8Hz,1H),7.08(d,J=9.2Hz, 1H), 4.81 (dd, J=11.7, 5.5Hz, 1H), 4.28 (t, J=12.1Hz, 1H), 3.27-2.98 (m, 2H), 2.05 (m, 1H).

[0083] 13 C NMR (100MHz, CDCl3) δ188.7,165.3,142.4,130.6,126.3(q,J=274.0Hz),124 .1,119.6,119.3,70.1(q,J=2.0Hz),40.2(q,J=2.0Hz),29.3(q,J=31.0Hz).

[0084] 19 F NMR (376MHz,CDCl3)δ-64.00.

[0085] Example 9

[0086] Compound 9: 6,8-dichloro-3-(2,2,2-trifluoroethyl)chroman-4-one, 6,8-dichloro-3-(2,2,2-trifluoroethyl)chroman-4-one, having the following structural formula;

[0087]

[0088] The steps are basically the same as those in Example 1, except that 2-allyloxy-3,5-dichlorobenzaldehyde is used to replace the 2-allyloxybenzaldehyde in Example 1. The yield is 87%.

[0089] 1 H NMR (400MHz, CDCl3) δ7.72(s,1H),7.52(s,1H),4.82(dd,J=11.7,5.3Hz,1H),4.24(t,J=12.1Hz,1H),3.20-2.96(m,2H),2.04(m,1H).

[0090] 13 C NMR (100MHz, CDCl3) δ188.9,155.7,135.9,127.1,126.5(q,J=275.0Hz),125 .6,123.9,121.5,70.3(q,J=2.0Hz),40.1(q,J=2.0Hz),29.4(q,J=30.0Hz)..

[0091] 19 F NMR (376MHz, CDCl3) δ-64.03.

[0092] Example 10

[0093] The steps are basically the same as those in Example 1, except that a 5W violet LED is used instead of an 8W violet LED. The yield is 82%.

[0094] Embodiment 11

[0095] The steps are basically the same as those in Example 1, except that a 10W violet LED is used instead of an 8W violet LED. The yield is 87%.

[0096] Example 12

[0097] The steps are basically the same as those in Example 1, except that an 8W blue LED is used instead of an 8W purple LED. The yield is 30%.

[0098] Embodiment 13

[0099] The steps are basically the same as those in Example 1, except that 0.39 mmol CF3SO2Na is used instead of 0.45 mmol CF3SO2Na. The yield is 83%.

[0100] Embodiment 14

[0101] The steps are basically the same as those in Example 1, except that 0.51 mmol CF3SO2Na is used instead of 0.45 mmol CF3SO2Na. The yield is 93%.

[0102] Embodiment 15

[0103] The steps are basically the same as those in Example 1, except that acetone is used instead of dimethyl sulfoxide. The yield is 45%.

[0104] Example 16

[0105] The steps are basically the same as those in Example 1, except that N,N-dimethylformamide (DMF) is used instead of dimethyl sulfoxide. The yield is 64%.

[0106] Embodiment 17

[0107] The steps are basically the same as those in Example 1, except that 1,2-dichloroethane is used instead of dimethyl sulfoxide. The yield is 55%.

[0108] Comparative Example 1

[0109] The steps were basically the same as in Example 1, except that ethanol was used instead of dimethyl sulfoxide. No reaction occurred.

[0110] Comparative Example 2

[0111] The steps are basically the same as those in Example 1, except that the irradiation with violet light at room temperature is replaced by the irradiation with no light at room temperature. No reaction occurs.

[0112] Comparative Example 3

[0113] The steps are basically the same as those in Example 1, except that the irradiation with purple light at room temperature is replaced by irradiation with no light at 60°C. No reaction occurs.

[0114] Comparative Example 4

[0115] The steps are basically the same as those in Example 1, except that the irradiation with purple light at room temperature is replaced by irradiation with no light at 100°C. No reaction occurs.

[0116] Comparative Example 5

[0117] The steps are basically the same as those in Example 1, except that an 8W yellow LED is used instead of an 8W purple LED. No reaction occurs.

[0118] Comparative Example 6

[0119] The steps are basically the same as those in Example 1, except that an 8W green LED is used instead of an 8W purple LED. No reaction occurs.

[0120] Comparative Example 7

[0121] The steps are basically the same as those in Example 1, except that an 8W white light LED is used instead of an 8W purple light LED. No reaction occurs.

[0122] The present invention investigates the effects of visible light of different colors on the reaction. By comparing the experimental results of Examples 1 and 12 with those of Comparative Examples 5 to 7, the experimental results show that: when irradiated by a yellow light source, a green light source, or a white light source, the reaction does not occur; when irradiated by a blue light source, the target product can be obtained but the yield is low; and when irradiated by a purple light source, the reaction effect is good, and the yield of the target product is significantly increased.

[0123] The present invention investigates the influence of different powers of the purple light source on the reaction. By comparing Examples 1, 10 to 11, the experimental results show that when the power of the purple light source is reduced from 8W to 5W, the reaction can proceed, but the yield of the target product obtained also decreases significantly. The yield of the target product reaches the highest value at 8W, which shows that increasing the power of the purple light source within a certain range can promote the occurrence of the reaction; but when the power of the purple light source is increased to 10W, it can be found that the yield of the target product does not increase but decreases, which shows that the excessive power of the purple light source is more conducive to the occurrence of side reactions and affects the yield of the target product. Therefore, 8W is selected as the optimal light source power of the purple light source for the reaction.

[0124] The present invention investigates the effect of the type of organic solvent on the reaction. By comparing Examples 1, 15 to 17 with Comparative Example 1, the experimental results show that when acetone, N,N-dimethylformamide or 1,2-dichloroethane is used as a solvent instead of dimethyl sulfoxide, the reaction can also occur, but the yield is low; but when ethanol is used as a solvent, the reaction does not occur. Therefore, dimethyl sulfoxide is selected as the best organic solvent for the reaction.

[0125] The present invention investigates whether visible light irradiation and temperature affect the reaction. By comparing Example 1 and Comparative Examples 2 to 4, the experimental results show that: when there is no violet LED irradiation, the reaction cannot proceed at room temperature; when there is no violet LED irradiation, when the temperature is increased from room temperature to 60°C or 100°C, the generation of the target product is not detected, that is, the reaction still does not occur. This shows that violet light irradiation is crucial to the occurrence of the reaction.

[0126] The present invention investigates the effect of the amount of sodium trifluoromethylsulfinate on the reaction. By comparing Examples 1, 13 and 14, the experimental results show that when the amount of sodium trifluoromethylsulfinate is reduced from 0.45mmol to 0.39mmol, the yield of the obtained target product is significantly reduced; when the amount of sodium trifluoromethylsulfinate is increased from 0.45mmol to 0.51mmol, the yield of the obtained target product is not significantly increased. Therefore, from the perspective of reaction cost, 0.45mmol is selected as the optimal reaction amount of sodium trifluoromethylsulfinate.

[0127] The present invention investigates R 1 The effect of the type and number of substituents on the reaction is shown in the comparison of Examples 1 to 9. The experimental results show that: 1 The type and number of substituents have little effect on the reaction of synthesizing trifluoromethyl-containing chroman-4-one compounds. 1 When the substituent is present, under appropriate conditions, the yield of the target product can reach more than 80%.

[0128] The present invention is not limited to the above-mentioned specific implementation modes. Various changes made by ordinary technicians in this field based on the above-mentioned concepts without creative work are all within the protection scope of the present invention.

Claims

1. A photocatalytic synthesis method of trifluoromethyl-containing chroman-4-one compounds, characterized in that: The following steps are involved: A 2-allyloxybenzaldehyde compound with a chemical structure shown in the general formula (I) and sodium trifluoromethylsulfinate are reacted in an organic solvent under visible light irradiation to obtain a trifluoromethyl-containing chroman-4-one compound with a general formula (II); Among them, R 1 The number of is 1 to 3, selected from hydrogen, C1 to C5 alkyl, C1 to C5 alkoxy, halogen, nitro or ester.

2. The photocatalytic synthesis method of trifluoromethyl-containing chroman-4-one compounds according to claim 1, characterized in that: The C1-C5 alkyl group is selected from any one of methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, isobutyl and trifluoromethyl; the C1-C5 alkoxy group is selected from methoxy, ethoxy, trifluoromethoxy or benzyloxy; the halogen group is selected from F, Cl or Br; the ester group is selected from methyl formate or ethyl formate.

3. The photocatalytic synthesis method of trifluoromethyl-containing chroman-4-one compounds according to claim 1, characterized in that: The molar ratio of the 2-allyloxybenzaldehyde compound to sodium trifluoromethanesulfinate is 1:1.3-1.

7.

4. The photocatalytic synthesis method of trifluoromethyl-containing chroman-4-one compounds according to claim 1, characterized in that: The visible light is purple light, and the purple light is provided by an LED purple light source with a power of 3 to 10W.

5. The photocatalytic synthesis method of trifluoromethyl-containing chroman-4-one compounds according to claim 1, characterized in that: The organic solvent is any one of N,N-dimethylformamide, dimethyl sulfoxide, acetone, ethyl acetate, 1,2-dichloroethane and tetrahydrofuran.

6. The photocatalytic synthesis method of trifluoromethyl-containing chroman-4-one compounds according to claim 1, characterized in that: The reaction is carried out at room temperature and the reaction time is 12 to 14 hours.

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